Reactions and Synthesis of Anticipated Biologically Active 2(1H) Pyridones synthesized from α, β-Unsaturated Carbonyl Compounds

Abstract

This work illustrates the versatile role of 2(1H)-pyridone moiety in the synthesis of different heterocyclic systems from readily obtainable materials. The work can be divided into three main parts: - i- Synthetic utility and chemical behaviour of 2-pyridone derivative. ii- Synthetic utility and chemical behaviour of 2-chloro -quinoline derivative. iii- Synthetic utility and chemical behaviour of 5-bromo-2-chloro-4,6-dimethylnicotinonitrile. First part: Synthetic utility and chemical behaviour of 2-pyridone derivative. Substituted 2-pyridones 1, 2 and 3 have been synthesized via one-pot multi-component reactions of an acetonitrile derivative (cyanoacetic ester, or cyanoacetamide) with heteroaromatic or aromatic aldehyde and a cyclic ketone in the presence of a basic catalyst in alcohol heated to its refluxing temperature. Reaction of compound 2 with ethyl chloroacetate in dry acetone in presence of anhydrous potassium carbonate afforded oxygen alkyl product 4. [cf. scheme I].